The uncritical exaggeration of digital devices use has recently revealed some negative outcomes on the developmental age and young adults, such as the de-humanisation of relationships and the de-materialisation of experiences. A comparison between the Montessori pedagogical tradition and current educational realities shows an undiminished childlike interest in freely chosen perceptual-sensory experiences. On these basis, children build up their personal knowledge and skills. This dimension also urges the training of educators, pedagogues and teachers who design learning experiences from their own cultural, educational and social backgrounds. An innovative methodological-didactic “experimentation” promoted within the SFBCT Department of the University of Macerata is based on this motivation. The initiative offered some seminars, workshop, guided tours at the Montessori House Museum and targeted qualitative observations at the Children’s House in Chiaravalle. The intent was to address the stated need and desire for direct experience, including relational experience, among students and between students and teachers.